Whatever happened to #3… Pennant, Freeman and Bendtner’s prolific strike partner

 #1   #2


Signed scholarship: Summer 1999. First-team apps: 26 (3 goals). Subsequent career: Birmingham City, Liverpool, Portsmouth (loan), Real Zaragoza, Stoke City (loan), Stoke City, Wolverhampton Wanderers (loan). 

Pennant joined Arsenal amid a blaze of publicity in 1999, as Arsenal paid a record £2 million fee for a teenager to prise him from Notts County. A Youth A Cup winner with Arsenal, he became the club’s youngest player when he made his debut against Middlesbrough, and, over the coming years, featured intermittently for the first-team, scoring a hat-trick against Southampton in 2003 on his full league debut. He spent much time away from the club on loan, first with Watford, then with Leeds United and Birmingham City before Arsenal finally let him join the latter on a permanent basis in 2005 following a raft of personal problems. After one season in the Midlands, Pennant looked to have resurrected his career at Liverpool, with whom he reached the Champions League Final in 2007, but, since leaving Anfield in 2009, he has failed to settle at any club and recently returned to Stoke City, his permanent employers, from a loan spell with Wolves.


Signed scholarship: Summer 2004. First-team apps: 8 (3 goals). Subsequent career: Fiorentina, Treviso (loan), Norwich City (loan), Sheffield United (loan), Ascoli, Grosseto. 

Italian striker Lupoli forged a formidable partnership with fellow forward Nicklas Bendtner after joining the club from Parma in 2004, scoring 25 goals in 32 appearances at Reserve and youth levels in his first season at the club. During that campaign, he also scored twice for the first-team in a Carling Cup victory over Everton, also finding the net in that competition against Reading the following season. After a loan spell at Derby County which yielded mixed results, he joined Fiorentina in a protracted move in 2007 and, following two loan spells back in England, now finds himself in Italy’s second tier with Grosseto. He has been capped by his country up to U21 level.


Signed scholarship: Summer 2008. First-team apps: 0. Subsequent career: Stevenage.

Another young striker who was highly-rated when he joined the club from Gillingham in 2008 having already made his senior debut, Freeman was regularly deployed on the left flank during his time with the Gunners, and was heavily involved in the Premier Academy League success of 2009/10. A hard worker and a willing runner, he was a frequent source of goals at Reserve and youth level, but found the path to the first-team too difficult to navigate and eventually joined Stevenage permanently last January following a successful loan spell at the Lamex Stadium. He has now made almost 80 senior appearances.




Signed scholarship: Summer 2007. First-team apps: 0. Subsequent career: Yeovil Town.

A resilient defender who progressed through the ranks of the Hale End Academy alongside Jack Wilshere and Emmanuel Frimpong, Ayling worked his way up to the cusp of the first-team squad, being named as a substitute for the Champions League trip to Olympiacos in 2009 having featured prominently in the club’s Premier Academy League and FA Youth Cup successes the previous season. He found subsequent call-ups hard to come by, however, and joined Yeovil Town for a short loan spell before making the move permanent in summer 2010. The affable youngster has since amassed over 100 appearances for the League One side.






Signed scholarship: Summer 2003. First-team apps: 0. Subsequent career: Boston United, Bishop’s Stortford, Boston United, Sleaford Town, Corby Town, Boston United, Stamford, Boston Town.

A goalkeeper who was named as a substitute for Arsenal against Manchester United in the League Cup, Wright has experienced a somewhat nomadic career since leaving Highbury following his release in 2005. He is currently with Boston Town in the United Counties League having played on three occasions for local rivals Boston United. Now 26, the Colchester-born stopper will be hopeful of one day working his way back into the Football League.




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